# Electronic Supplementary Material (ESI) for Analytical Methods.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nar

_audit_creation_date             2013-12-07T19:02:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C2.11 H2.39 N0.42 O0.70'
_chemical_formula_weight         44.82

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C c'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_Int_Tables_number      9
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   23.380(3)
_cell_length_b                   6.9690(7)
_cell_length_c                   19.937(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.851(15)
_cell_angle_gamma                90
_cell_volume                     3035.7(7)
_cell_formula_units_Z            57
_cell_measurement_temperature    293(2)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             1344
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_number            6184
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.068
_diffrn_reflns_theta_max         29.062
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.847
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_point_group_measured_fraction_full 0.634
_diffrn_reflns_point_group_measured_fraction_max 0.518
_reflns_number_total             4217
_reflns_number_gt                3368
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+0.2153P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0010(2)
_refine_ls_number_reflns         4217
_refine_ls_number_parameters     552
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0906
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 622 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(7)
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.33939(11) 0.3425(4) 0.24004(14) 0.0636(7) Uani 1 d . .
N1 N 0.62429(13) 0.2564(4) 0.33906(16) 0.0449(6) Uani 1 d . .
C1 C 0.8778(2) 0.2853(9) 0.3858(3) 0.0761(13) Uani 1 d . .
O2 O 0.07654(13) 0.2195(4) 0.25846(15) 0.0702(8) Uani 1 d . .
N2 N 0.58310(13) 0.2181(4) 0.27561(17) 0.0459(6) Uani 1 d . .
C2 C 0.7911(2) 0.5117(6) 0.3358(3) 0.0653(11) Uani 1 d . .
O3 O -0.28532(12) 0.4432(4) 0.14856(14) 0.0696(7) Uani 1 d . .
N3 N 0.48883(16) 0.1996(4) 0.13163(17) 0.0558(8) Uani 1 d . .
C3 C 0.80908(15) 0.3127(5) 0.3673(2) 0.0504(8) Uani 1 d . .
O4 O -0.25272(11) 0.1782(4) -0.05255(14) 0.0602(6) Uani 1 d . .
N4 N -0.06286(15) 0.1819(4) 0.01307(16) 0.0606(8) Uani 1 d . .
C4 C 0.79263(17) 0.2852(6) 0.4339(2) 0.0561(9) Uani 1 d . .
O5 O 0.67137(12) 0.1218(4) 0.23344(15) 0.0687(7) Uani 1 d . .
N5 N -0.16292(13) 0.2499(4) 0.06691(16) 0.0455(7) Uani 1 d . .
C5 C 0.72551(16) 0.2852(4) 0.4224(2) 0.0484(8) Uani 1 d . .
O6 O 0.54091(13) 0.1579(4) 0.13671(16) 0.0778(8) Uani 1 d . .
N6 N -0.20430(12) 0.3065(4) 0.09340(14) 0.0456(6) Uani 1 d . .
C6 C 0.68258(16) 0.2344(4) 0.3489(2) 0.0453(8) Uani 1 d . .
O7 O -0.01813(14) 0.1685(6) -0.00448(17) 0.1031(12) Uani 1 d . .
C7 C 0.70627(17) 0.1690(4) 0.2936(2) 0.0516(9) Uani 1 d . .
O8 O 0.70720(12) 0.3248(4) 0.47037(14) 0.0651(7) Uani 1 d . .
C8 C 0.77424(18) 0.1604(6) 0.3123(3) 0.0599(10) Uani 1 d . .
C9 C 0.52133(16) 0.2456(4) 0.26425(19) 0.0415(7) Uani 1 d . .
O10 O 0.44736(16) 0.2068(5) 0.07377(16) 0.0922(10) Uani 1 d . .
C10 C 0.50194(17) 0.2819(5) 0.32214(19) 0.0484(8) Uani 1 d . .
O11 O -0.11489(13) 0.1715(5) -0.03077(15) 0.0757(8) Uani 1 d . .
C11 C 0.44235(17) 0.3113(5) 0.3128(2) 0.0527(8) Uani 1 d . .
C12 C 0.39716(15) 0.3046(4) 0.24387(19) 0.0466(8) Uani 1 d . .
C13 C 0.41408(17) 0.2673(4) 0.1857(2) 0.0450(8) Uani 1 d . .
C14 C 0.47563(15) 0.2379(4) 0.19636(18) 0.0427(8) Uani 1 d . .
C15 C 0.29180(19) 0.3307(8) 0.1714(3) 0.0703(12) Uani 1 d . .
C16 C 0.1265(2) 0.1839(7) 0.2349(3) 0.0737(13) Uani 1 d . .
C17 C 0.01967(16) 0.2246(4) 0.2079(2) 0.0503(9) Uani 1 d . .
C19 C -0.08664(16) 0.2695(4) 0.18656(18) 0.0463(8) Uani 1 d . .
C18 C -0.02770(18) 0.2601(5) 0.2331(2) 0.0513(9) Uani 1 d . .
C20 C -0.10194(15) 0.2423(4) 0.11262(17) 0.0399(7) Uani 1 d . .
C25 C -0.37194(16) 0.3612(5) 0.0462(2) 0.0522(9) Uani 1 d . .
C24 C -0.30444(15) 0.3740(5) 0.08878(18) 0.0466(8) Uani 1 d . .
C23 C -0.26254(15) 0.3019(4) 0.05279(18) 0.0430(7) Uani 1 d . .
C22 C 0.00716(16) 0.1973(5) 0.1359(2) 0.0496(8) Uani 1 d . .
C21 C -0.05339(15) 0.2070(4) 0.08897(17) 0.0437(8) Uani 1 d . .
C26 C -0.39031(14) 0.1994(5) -0.00792(18) 0.0445(7) Uani 1 d . .
C28 C -0.28638(15) 0.2311(4) -0.02128(19) 0.0442(7) Uani 1 d . .
C27 C -0.35488(16) 0.2228(6) -0.0588(2) 0.0514(9) Uani 1 d . .
C29 C -0.45879(17) 0.2129(7) -0.0515(3) 0.0631(11) Uani 1 d . .
C30 C -0.3764(2) 0.0067(6) 0.0295(3) 0.0603(9) Uani 1 d . .
H001 H -0.3666(16) 0.122(5) -0.093(2) 0.065(11) Uiso 1 d . .
H002 H 0.2991(15) 0.419(5) 0.134(2) 0.058(10) Uiso 1 d . .
H003 H 0.8117(18) 0.382(6) 0.469(2) 0.067(12) Uiso 1 d . .
H004 H 0.1275(19) 0.284(6) 0.197(3) 0.084(14) Uiso 1 d . .
H005 H -0.3940(16) 0.365(5) 0.078(2) 0.060(10) Uiso 1 d . .
H006 H 0.4286(16) 0.334(4) 0.357(2) 0.057(10) Uiso 1 d . .
H007 H -0.3839(16) 0.486(5) 0.0198(18) 0.059(10) Uiso 1 d . .
H008 H 0.8099(18) 0.158(5) 0.456(2) 0.072(12) Uiso 1 d . .
H009 H 0.815(2) 0.604(6) 0.370(2) 0.072(12) Uiso 1 d . .
H010 H 0.1231(19) 0.050(6) 0.213(2) 0.080(12) Uiso 1 d . .
H011 H 0.0393(16) 0.177(5) 0.116(2) 0.056(10) Uiso 1 d . .
H012 H 0.799(2) 0.521(6) 0.292(3) 0.095(15) Uiso 1 d . .
H013 H -0.399(2) -0.019(6) 0.061(2) 0.088(13) Uiso 1 d . .
H014 H -0.334(2) -0.006(6) 0.063(2) 0.085(13) Uiso 1 d . .
H015 H -0.1734(18) 0.210(5) 0.021(2) 0.059(11) Uiso 1 d . .
H016 H -0.0185(17) 0.282(5) 0.281(2) 0.053(10) Uiso 1 d . .
H017 H 0.5937(17) 0.172(5) 0.237(2) 0.058(10) Uiso 1 d . .
H018 H -0.3679(16) 0.350(5) -0.082(2) 0.062(11) Uiso 1 d . .
H019 H -0.1181(16) 0.292(4) 0.207(2) 0.050(9) Uiso 1 d . .
H020 H 0.899(2) 0.380(6) 0.420(3) 0.091(16) Uiso 1 d . .
H21 H 0.3834(15) 0.261(4) 0.138(2) 0.044(9) Uiso 1 d . .
H22 H -0.472(2) 0.343(6) -0.074(3) 0.098(16) Uiso 1 d . .
H23 H -0.4755(18) 0.104(6) -0.086(2) 0.076(12) Uiso 1 d . .
H24 H 0.7875(17) 0.034(6) 0.335(2) 0.072(12) Uiso 1 d . .
H25 H 0.749(2) 0.541(6) 0.328(2) 0.092(14) Uiso 1 d . .
H26 H 0.887(2) 0.315(6) 0.344(3) 0.100(16) Uiso 1 d . .
H27 H -0.481(2) 0.195(6) -0.024(3) 0.094(16) Uiso 1 d . .
H28 H 0.7811(16) 0.179(5) 0.266(2) 0.059(10) Uiso 1 d . .
H29 H 0.293(2) 0.212(7) 0.147(3) 0.092(15) Uiso 1 d . .
H30 H 0.5333(16) 0.286(4) 0.368(2) 0.048(10) Uiso 1 d . .
H31 H 0.160(3) 0.186(7) 0.274(4) 0.12(2) Uiso 1 d . .
H32 H 0.254(2) 0.365(6) 0.181(2) 0.087(13) Uiso 1 d . .
H33 H -0.389(2) -0.102(8) 0.000(3) 0.107(17) Uiso 1 d . .
H34 H 0.887(2) 0.148(7) 0.398(3) 0.100(17) Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.352(4) . ?
O1 C15 1.426(5) . ?
N1 C6 1.315(4) . ?
N1 N2 1.316(4) . ?
C1 C3 1.526(5) . ?
C1 H020 0.95(5) . ?
C1 H26 0.96(6) . ?
C1 H34 0.99(5) . ?
O2 C17 1.353(4) . ?
O2 C16 1.427(6) . ?
N2 C9 1.393(4) . ?
N2 H017 0.94(4) . ?
C2 C3 1.519(5) . ?
C2 H009 0.95(5) . ?
C2 H012 0.95(5) . ?
C2 H25 0.97(4) . ?
O3 C24 1.214(4) . ?
N3 O10 1.215(4) . ?
N3 O6 1.221(4) . ?
N3 C14 1.455(4) . ?
C3 C4 1.521(5) . ?
C3 C8 1.536(5) . ?
O4 C28 1.222(4) . ?
N4 O7 1.219(4) . ?
N4 O11 1.221(4) . ?
N4 C21 1.460(4) . ?
C4 C5 1.503(5) . ?
C4 H003 0.95(4) . ?
C4 H008 1.01(4) . ?
O5 C7 1.231(4) . ?
N5 N6 1.317(4) . ?
N5 C20 1.393(4) . ?
N5 H015 0.91(4) . ?
C5 O8 1.211(4) . ?
C5 C6 1.494(5) . ?
N6 C23 1.314(4) . ?
C6 C7 1.472(5) . ?
C7 C8 1.499(5) . ?
C8 H24 0.99(4) . ?
C8 H28 1.00(4) . ?
C9 C14 1.395(4) . ?
C9 C10 1.405(5) . ?
C10 C11 1.354(5) . ?
C10 H30 0.95(4) . ?
C11 C12 1.405(5) . ?
C11 H006 1.06(4) . ?
C12 C13 1.378(5) . ?
C13 C14 1.393(5) . ?
C13 H21 0.97(4) . ?
C15 H002 1.03(4) . ?
C15 H29 0.96(5) . ?
C15 H32 1.01(4) . ?
C16 H004 1.04(5) . ?
C16 H010 1.02(4) . ?
C16 H31 0.89(6) . ?
C17 C22 1.372(5) . ?
C17 C18 1.391(5) . ?
C19 C18 1.361(5) . ?
C19 C20 1.401(4) . ?
C19 H019 0.97(4) . ?
C18 H016 0.91(4) . ?
C20 C21 1.397(5) . ?
C25 C24 1.505(5) . ?
C25 C26 1.513(5) . ?
C25 H005 0.95(4) . ?
C25 H007 1.00(4) . ?
C24 C23 1.492(4) . ?
C23 C28 1.466(5) . ?
C22 C21 1.393(5) . ?
C22 H011 0.97(4) . ?
C26 C30 1.515(5) . ?
C26 C29 1.529(5) . ?
C26 C27 1.529(5) . ?
C28 C27 1.508(5) . ?
C27 H001 0.95(4) . ?
C27 H018 0.99(4) . ?
C29 H22 1.01(5) . ?
C29 H23 1.01(4) . ?
C29 H27 0.89(5) . ?
C30 H013 0.98(5) . ?
C30 H014 0.98(4) . ?
C30 H33 0.94(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 C15 117.7(3) . . ?
C6 N1 N2 119.0(3) . . ?
C3 C1 H020 108(3) . . ?
C3 C1 H26 108(3) . . ?
H020 C1 H26 105(4) . . ?
C3 C1 H34 107(3) . . ?
H020 C1 H34 119(4) . . ?
H26 C1 H34 110(4) . . ?
C17 O2 C16 117.5(3) . . ?
N1 N2 C9 119.3(3) . . ?
N1 N2 H017 123(2) . . ?
C9 N2 H017 118(2) . . ?
C3 C2 H009 108(2) . . ?
C3 C2 H012 109(3) . . ?
H009 C2 H012 110(4) . . ?
C3 C2 H25 112(3) . . ?
H009 C2 H25 106(3) . . ?
H012 C2 H25 112(4) . . ?
O10 N3 O6 121.6(3) . . ?
O10 N3 C14 119.0(3) . . ?
O6 N3 C14 119.4(3) . . ?
C2 C3 C4 111.0(3) . . ?
C2 C3 C1 109.1(4) . . ?
C4 C3 C1 110.2(3) . . ?
C2 C3 C8 109.7(3) . . ?
C4 C3 C8 107.6(3) . . ?
C1 C3 C8 109.3(3) . . ?
O7 N4 O11 121.8(3) . . ?
O7 N4 C21 118.5(3) . . ?
O11 N4 C21 119.6(3) . . ?
C5 C4 C3 116.2(3) . . ?
C5 C4 H003 108(2) . . ?
C3 C4 H003 110(2) . . ?
C5 C4 H008 107(2) . . ?
C3 C4 H008 108(2) . . ?
H003 C4 H008 107(3) . . ?
N6 N5 C20 118.4(3) . . ?
N6 N5 H015 122(2) . . ?
C20 N5 H015 120(2) . . ?
O8 C5 C6 121.7(3) . . ?
O8 C5 C4 121.5(3) . . ?
C6 C5 C4 116.8(3) . . ?
C23 N6 N5 119.6(3) . . ?
N1 C6 C7 124.8(3) . . ?
N1 C6 C5 114.7(3) . . ?
C7 C6 C5 120.5(3) . . ?
O5 C7 C6 121.1(3) . . ?
O5 C7 C8 120.5(3) . . ?
C6 C7 C8 118.3(3) . . ?
C7 C8 C3 113.3(3) . . ?
C7 C8 H24 106(2) . . ?
C3 C8 H24 107(2) . . ?
C7 C8 H28 106(2) . . ?
C3 C8 H28 111(2) . . ?
H24 C8 H28 114(3) . . ?
N2 C9 C14 123.0(3) . . ?
N2 C9 C10 120.7(3) . . ?
C14 C9 C10 116.4(3) . . ?
C11 C10 C9 122.1(3) . . ?
C11 C10 H30 122(2) . . ?
C9 C10 H30 116(2) . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H006 121(2) . . ?
C12 C11 H006 119(2) . . ?
O1 C12 C13 124.8(3) . . ?
O1 C12 C11 115.9(3) . . ?
C13 C12 C11 119.3(3) . . ?
C12 C13 C14 119.3(3) . . ?
C12 C13 H21 120(2) . . ?
C14 C13 H21 120(2) . . ?
C13 C14 C9 122.4(3) . . ?
C13 C14 N3 115.2(3) . . ?
C9 C14 N3 122.5(3) . . ?
O1 C15 H002 113(2) . . ?
O1 C15 H29 113(3) . . ?
H002 C15 H29 96(4) . . ?
O1 C15 H32 104(3) . . ?
H002 C15 H32 112(3) . . ?
H29 C15 H32 119(4) . . ?
O2 C16 H004 111(2) . . ?
O2 C16 H010 110(2) . . ?
H004 C16 H010 109(3) . . ?
O2 C16 H31 107(4) . . ?
H004 C16 H31 113(4) . . ?
H010 C16 H31 107(4) . . ?
O2 C17 C22 124.2(3) . . ?
O2 C17 C18 115.7(3) . . ?
C22 C17 C18 120.1(3) . . ?
C18 C19 C20 121.8(3) . . ?
C18 C19 H019 117(2) . . ?
C20 C19 H019 121(2) . . ?
C19 C18 C17 120.4(4) . . ?
C19 C18 H016 121(2) . . ?
C17 C18 H016 119(2) . . ?
N5 C20 C21 123.4(3) . . ?
N5 C20 C19 120.1(3) . . ?
C21 C20 C19 116.4(3) . . ?
C24 C25 C26 114.9(3) . . ?
C24 C25 H005 109(2) . . ?
C26 C25 H005 114(2) . . ?
C24 C25 H007 107(2) . . ?
C26 C25 H007 109(2) . . ?
H005 C25 H007 102(3) . . ?
O3 C24 C23 122.0(3) . . ?
O3 C24 C25 121.5(3) . . ?
C23 C24 C25 116.4(3) . . ?
N6 C23 C28 124.6(3) . . ?
N6 C23 C24 114.2(3) . . ?
C28 C23 C24 121.2(3) . . ?
C17 C22 C21 118.9(3) . . ?
C17 C22 H011 122(2) . . ?
C21 C22 H011 119(2) . . ?
C22 C21 C20 122.4(3) . . ?
C22 C21 N4 115.7(3) . . ?
C20 C21 N4 122.0(3) . . ?
C25 C26 C30 110.7(3) . . ?
C25 C26 C29 109.5(3) . . ?
C30 C26 C29 109.4(3) . . ?
C25 C26 C27 108.1(3) . . ?
C30 C26 C27 110.5(3) . . ?
C29 C26 C27 108.8(3) . . ?
O4 C28 C23 122.2(3) . . ?
O4 C28 C27 119.9(3) . . ?
C23 C28 C27 117.9(3) . . ?
C28 C27 C26 114.0(3) . . ?
C28 C27 H001 112(2) . . ?
C26 C27 H001 108(2) . . ?
C28 C27 H018 107(2) . . ?
C26 C27 H018 105(2) . . ?
H001 C27 H018 111(3) . . ?
C26 C29 H22 114(3) . . ?
C26 C29 H23 115(2) . . ?
H22 C29 H23 112(4) . . ?
C26 C29 H27 111(3) . . ?
H22 C29 H27 104(4) . . ?
H23 C29 H27 99(4) . . ?
C26 C30 H013 114(2) . . ?
C26 C30 H014 114(2) . . ?
H013 C30 H014 101(3) . . ?
C26 C30 H33 116(3) . . ?
H013 C30 H33 98(4) . . ?
H014 C30 H33 111(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 N2 C9 -178.5(3) . . . . ?
C2 C3 C4 C5 65.9(4) . . . . ?
C1 C3 C4 C5 -173.2(4) . . . . ?
C8 C3 C4 C5 -54.1(4) . . . . ?
C3 C4 C5 O8 -156.4(3) . . . . ?
C3 C4 C5 C6 23.5(5) . . . . ?
C20 N5 N6 C23 -175.2(3) . . . . ?
N2 N1 C6 C7 0.1(4) . . . . ?
N2 N1 C6 C5 178.9(3) . . . . ?
O8 C5 C6 N1 7.0(4) . . . . ?
C4 C5 C6 N1 -172.9(3) . . . . ?
O8 C5 C6 C7 -174.1(3) . . . . ?
C4 C5 C6 C7 6.0(4) . . . . ?
N1 C6 C7 O5 -3.2(5) . . . . ?
C5 C6 C7 O5 178.0(3) . . . . ?
N1 C6 C7 C8 177.1(3) . . . . ?
C5 C6 C7 C8 -1.7(4) . . . . ?
O5 C7 C8 C3 149.1(3) . . . . ?
C6 C7 C8 C3 -31.1(5) . . . . ?
C2 C3 C8 C7 -63.5(4) . . . . ?
C4 C3 C8 C7 57.3(4) . . . . ?
C1 C3 C8 C7 176.9(4) . . . . ?
N1 N2 C9 C14 169.6(3) . . . . ?
N1 N2 C9 C10 -10.8(4) . . . . ?
N2 C9 C10 C11 179.3(3) . . . . ?
C14 C9 C10 C11 -1.1(4) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C15 O1 C12 C13 4.3(5) . . . . ?
C15 O1 C12 C11 -177.9(3) . . . . ?
C10 C11 C12 O1 -177.8(3) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
O1 C12 C13 C14 177.4(3) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 C9 -0.3(4) . . . . ?
C12 C13 C14 N3 180.0(3) . . . . ?
N2 C9 C14 C13 -179.5(3) . . . . ?
C10 C9 C14 C13 0.9(4) . . . . ?
N2 C9 C14 N3 0.3(4) . . . . ?
C10 C9 C14 N3 -179.3(3) . . . . ?
O10 N3 C14 C13 4.3(4) . . . . ?
O6 N3 C14 C13 -174.5(3) . . . . ?
O10 N3 C14 C9 -175.4(3) . . . . ?
O6 N3 C14 C9 5.8(5) . . . . ?
C16 O2 C17 C22 0.2(5) . . . . ?
C16 O2 C17 C18 -179.9(3) . . . . ?
C20 C19 C18 C17 0.6(5) . . . . ?
O2 C17 C18 C19 179.6(3) . . . . ?
C22 C17 C18 C19 -0.5(5) . . . . ?
N6 N5 C20 C21 -172.0(3) . . . . ?
N6 N5 C20 C19 8.4(4) . . . . ?
C18 C19 C20 N5 178.9(3) . . . . ?
C18 C19 C20 C21 -0.6(4) . . . . ?
C26 C25 C24 O3 -152.8(3) . . . . ?
C26 C25 C24 C23 28.7(4) . . . . ?
N5 N6 C23 C28 2.1(5) . . . . ?
N5 N6 C23 C24 -178.7(3) . . . . ?
O3 C24 C23 N6 5.0(5) . . . . ?
C25 C24 C23 N6 -176.6(3) . . . . ?
O3 C24 C23 C28 -175.7(3) . . . . ?
C25 C24 C23 C28 2.7(4) . . . . ?
O2 C17 C22 C21 -179.6(3) . . . . ?
C18 C17 C22 C21 0.4(5) . . . . ?
C17 C22 C21 C20 -0.5(5) . . . . ?
C17 C22 C21 N4 178.3(3) . . . . ?
N5 C20 C21 C22 -179.0(3) . . . . ?
C19 C20 C21 C22 0.6(4) . . . . ?
N5 C20 C21 N4 2.3(4) . . . . ?
C19 C20 C21 N4 -178.2(3) . . . . ?
O7 N4 C21 C22 -5.2(5) . . . . ?
O11 N4 C21 C22 173.5(3) . . . . ?
O7 N4 C21 C20 173.6(3) . . . . ?
O11 N4 C21 C20 -7.7(5) . . . . ?
C24 C25 C26 C30 64.0(4) . . . . ?
C24 C25 C26 C29 -175.3(3) . . . . ?
C24 C25 C26 C27 -57.0(4) . . . . ?
N6 C23 C28 O4 -3.6(5) . . . . ?
C24 C23 C28 O4 177.2(3) . . . . ?
N6 C23 C28 C27 175.8(3) . . . . ?
C24 C23 C28 C27 -3.4(5) . . . . ?
O4 C28 C27 C26 152.5(3) . . . . ?
C23 C28 C27 C26 -26.9(5) . . . . ?
C25 C26 C27 C28 55.7(4) . . . . ?
C30 C26 C27 C28 -65.4(4) . . . . ?
C29 C26 C27 C28 174.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C16 H004 O5 1.04(5) 2.57(4) 3.230(6) 121(3) 3_455
C11 H006 O7 1.06(4) 2.59(4) 3.427(5) 136(2) 4
N5 H015 O4 0.91(4) 1.92(4) 2.602(4) 130(3) .
N5 H015 O11 0.91(4) 2.00(4) 2.628(4) 125(3) .
N2 H017 O5 0.94(4) 1.88(4) 2.579(4) 129(3) .
N2 H017 O6 0.94(4) 1.94(4) 2.622(4) 127(3) .
C15 H29 O3 0.96(5) 2.62(5) 3.189(6) 118(3) 3_545
C16 H004 O5 1.04(5) 2.57(4) 3.230(6) 121(3) 3_455
C25 H005 O6 0.95(4) 2.65(4) 3.469(5) 144(3) 1_455
C11 H006 O7 1.06(4) 2.59(4) 3.427(5) 136(2) 4
N5 H015 O4 0.91(4) 1.92(4) 2.602(4) 130(3) .
N5 H015 O11 0.91(4) 2.00(4) 2.628(4) 125(3) .
N2 H017 O5 0.94(4) 1.88(4) 2.579(4) 129(3) .
N2 H017 O6 0.94(4) 1.94(4) 2.622(4) 127(3) .
C15 H29 O3 0.96(5) 2.62(5) 3.189(6) 118(3) 3_545

# The following lines are used to test the character set of files sent by
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# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 977177'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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data_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 N3 O4'
_chemical_formula_weight         303.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.628(5)
_cell_length_b                   6.8734(11)
_cell_length_c                   21.792(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.39(3)
_cell_angle_gamma                90
_cell_volume                     2926.7(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.800
_exptl_crystal_size_min          0.600
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.942
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5858
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.142
_diffrn_reflns_theta_max         28.990
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3328
_reflns_number_gt                1982
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+0.3204P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0006(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3328
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1339
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.044
_refine_ls_shift/su_mean         0.003

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.57315(9) 0.8201(2) 0.60734(8) 0.0402(4) Uani 1 1 d . . . . .
N3 N 0.42945(9) 0.8018(2) 0.50881(9) 0.0454(4) Uani 1 1 d . . . . .
N2 N 0.63833(8) 0.8260(2) 0.65043(8) 0.0397(4) Uani 1 1 d . . . . .
O1 O 0.44126(8) 0.8321(2) 0.56804(8) 0.0620(5) Uani 1 1 d . . . . .
O4 O 0.77180(8) 0.8468(2) 0.73770(8) 0.0597(5) Uani 1 1 d . . . . .
O2 O 0.37189(8) 0.8110(3) 0.46305(8) 0.0698(5) Uani 1 1 d . . . . .
O3 O 0.54438(8) 0.9368(3) 0.70325(7) 0.0673(5) Uani 1 1 d . . . . .
C7 C 0.55395(10) 0.7650(3) 0.54044(9) 0.0373(5) Uani 1 1 d . . . . .
C8 C 0.65491(10) 0.8812(3) 0.71312(10) 0.0379(5) Uani 1 1 d . . . . .
C1 C 0.48603(10) 0.7558(2) 0.49204(10) 0.0384(5) Uani 1 1 d . . . . .
C10 C 0.75120(12) 0.9241(4) 0.83277(11) 0.0493(6) Uani 1 1 d . . . . .
C11 C 0.69763(10) 0.8953(3) 0.85946(10) 0.0444(5) Uani 1 1 d . . . . .
C2 C 0.46856(12) 0.7010(3) 0.42529(11) 0.0448(5) Uani 1 1 d . . . . .
C5 C 0.58518(13) 0.6653(3) 0.45197(11) 0.0502(6) Uani 1 1 d . . . . .
C3 C 0.51728(13) 0.6546(3) 0.40411(11) 0.0483(6) Uani 1 1 d . . . . .
C9 C 0.72979(11) 0.8793(3) 0.75926(10) 0.0428(5) Uani 1 1 d . . . . .
C13 C 0.60596(11) 0.9386(3) 0.73974(10) 0.0458(5) Uani 1 1 d . . . . .
C12 C 0.63331(12) 1.0025(4) 0.81195(11) 0.0491(6) Uani 1 1 d . . . . .
C6 C 0.60340(12) 0.7188(3) 0.51795(11) 0.0451(5) Uani 1 1 d . . . . .
C15 C 0.72352(15) 0.9819(5) 0.93049(13) 0.0632(7) Uani 1 1 d . . . . .
C4 C 0.4990(2) 0.5943(5) 0.33223(14) 0.0678(8) Uani 1 1 d . . . . .
C14 C 0.68228(17) 0.6809(4) 0.86216(16) 0.0648(7) Uani 1 1 d . . . . .
H2 H 0.4228(10) 0.700(3) 0.3965(9) 0.039(5) Uiso 1 1 d . . . . .
H6 H 0.6478(11) 0.729(3) 0.5482(10) 0.047(6) Uiso 1 1 d . . . . .
H10A H 0.7903(14) 0.848(3) 0.8575(12) 0.083(8) Uiso 1 1 d . . . . .
H1 H 0.5400(13) 0.853(3) 0.6223(11) 0.070(7) Uiso 1 1 d . . . . .
H15A H 0.7301(15) 1.126(4) 0.9308(13) 0.093(10) Uiso 1 1 d . . . . .
H14A H 0.6494(13) 0.664(3) 0.8779(11) 0.070(8) Uiso 1 1 d . . . . .
H5 H 0.6185(11) 0.635(3) 0.4381(10) 0.050(6) Uiso 1 1 d . . . . .
H12A H 0.5967(11) 0.998(3) 0.8263(10) 0.058(6) Uiso 1 1 d . . . . .
H10B H 0.7656(13) 1.068(4) 0.8375(12) 0.085(8) Uiso 1 1 d . . . . .
H12B H 0.6437(12) 1.142(3) 0.8116(11) 0.065(7) Uiso 1 1 d . . . . .
H14B H 0.7252(14) 0.610(4) 0.8925(13) 0.083(9) Uiso 1 1 d . . . . .
H15B H 0.6890(13) 0.974(3) 0.9488(12) 0.075(8) Uiso 1 1 d . . . . .
H15C H 0.7648(14) 0.918(3) 0.9616(12) 0.078(8) Uiso 1 1 d . . . . .
H14C H 0.6690(12) 0.615(3) 0.8171(13) 0.076(8) Uiso 1 1 d . . . . .
H4A H 0.4517(19) 0.585(5) 0.3085(16) 0.120(13) Uiso 1 1 d . . . . .
H4B H 0.5080(15) 0.694(4) 0.3081(14) 0.101(10) Uiso 1 1 d . . . . .
H4C H 0.5128(16) 0.467(5) 0.3278(15) 0.110(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.318(2) . ?
N1 C7 1.386(2) . ?
N1 H1 0.93(2) . ?
N3 O2 1.218(2) . ?
N3 O1 1.222(2) . ?
N3 C1 1.454(2) . ?
N2 C8 1.311(2) . ?
O4 C9 1.209(2) . ?
O3 C13 1.224(2) . ?
C7 C6 1.391(3) . ?
C7 C1 1.395(3) . ?
C8 C13 1.463(3) . ?
C8 C9 1.496(3) . ?
C1 C2 1.389(3) . ?
C10 C9 1.497(3) . ?
C10 C11 1.516(3) . ?
C10 H10A 0.94(3) . ?
C10 H10B 1.03(3) . ?
C11 C14 1.518(3) . ?
C11 C12 1.521(3) . ?
C11 C15 1.523(3) . ?
C2 C3 1.357(3) . ?
C2 H2 0.92(2) . ?
C5 C6 1.368(3) . ?
C5 C3 1.392(3) . ?
C5 H5 0.92(2) . ?
C3 C4 1.500(3) . ?
C13 C12 1.490(3) . ?
C12 H12A 0.97(2) . ?
C12 H12B 0.99(2) . ?
C6 H6 0.90(2) . ?
C15 H15A 1.00(3) . ?
C15 H15B 0.99(3) . ?
C15 H15C 0.96(3) . ?
C4 H4A 0.93(3) . ?
C4 H4B 0.94(3) . ?
C4 H4C 0.94(3) . ?
C14 H14A 0.92(2) . ?
C14 H14B 1.01(3) . ?
C14 H14C 1.00(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C7 120.30(17) . . ?
N2 N1 H1 119.4(14) . . ?
C7 N1 H1 120.3(14) . . ?
O2 N3 O1 122.24(18) . . ?
O2 N3 C1 118.71(18) . . ?
O1 N3 C1 119.04(17) . . ?
C8 N2 N1 118.86(17) . . ?
N1 C7 C6 120.27(19) . . ?
N1 C7 C1 123.45(18) . . ?
C6 C7 C1 116.27(19) . . ?
N2 C8 C13 124.77(18) . . ?
N2 C8 C9 115.57(17) . . ?
C13 C8 C9 119.65(18) . . ?
C2 C1 C7 122.00(19) . . ?
C2 C1 N3 116.21(19) . . ?
C7 C1 N3 121.79(17) . . ?
C9 C10 C11 116.57(18) . . ?
C9 C10 H10A 106.7(15) . . ?
C11 C10 H10A 110.7(15) . . ?
C9 C10 H10B 104.3(13) . . ?
C11 C10 H10B 109.6(14) . . ?
H10A C10 H10B 109(2) . . ?
C10 C11 C14 111.0(2) . . ?
C10 C11 C12 107.58(18) . . ?
C14 C11 C12 110.2(2) . . ?
C10 C11 C15 109.30(19) . . ?
C14 C11 C15 109.3(2) . . ?
C12 C11 C15 109.5(2) . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 122.2(12) . . ?
C1 C2 H2 116.6(12) . . ?
C6 C5 C3 122.5(2) . . ?
C6 C5 H5 119.6(13) . . ?
C3 C5 H5 117.8(13) . . ?
C2 C3 C5 117.1(2) . . ?
C2 C3 C4 121.6(2) . . ?
C5 C3 C4 121.2(2) . . ?
O4 C9 C8 121.18(19) . . ?
O4 C9 C10 120.98(19) . . ?
C8 C9 C10 117.82(18) . . ?
O3 C13 C8 120.69(19) . . ?
O3 C13 C12 121.19(19) . . ?
C8 C13 C12 118.11(19) . . ?
C13 C12 C11 114.16(18) . . ?
C13 C12 H12A 108.7(12) . . ?
C11 C12 H12A 113.5(12) . . ?
C13 C12 H12B 105.4(13) . . ?
C11 C12 H12B 109.4(14) . . ?
H12A C12 H12B 104.9(18) . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 121.6(13) . . ?
C7 C6 H6 117.5(13) . . ?
C11 C15 H15A 112.5(15) . . ?
C11 C15 H15B 112.1(14) . . ?
H15A C15 H15B 101(2) . . ?
C11 C15 H15C 111.4(15) . . ?
H15A C15 H15C 111(2) . . ?
H15B C15 H15C 109(2) . . ?
C3 C4 H4A 110(2) . . ?
C3 C4 H4B 111.0(17) . . ?
H4A C4 H4B 101(3) . . ?
C3 C4 H4C 114.2(18) . . ?
H4A C4 H4C 101(3) . . ?
H4B C4 H4C 118(3) . . ?
C11 C14 H14A 110.7(15) . . ?
C11 C14 H14B 109.9(15) . . ?
H14A C14 H14B 110(2) . . ?
C11 C14 H14C 111.9(13) . . ?
H14A C14 H14C 111(2) . . ?
H14B C14 H14C 103(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C8 179.09(16) . . . . ?
N2 N1 C7 C6 -1.1(3) . . . . ?
N2 N1 C7 C1 -179.89(17) . . . . ?
N1 N2 C8 C13 -0.2(3) . . . . ?
N1 N2 C8 C9 178.58(16) . . . . ?
N1 C7 C1 C2 179.64(17) . . . . ?
C6 C7 C1 C2 0.8(3) . . . . ?
N1 C7 C1 N3 -0.8(3) . . . . ?
C6 C7 C1 N3 -179.57(16) . . . . ?
O2 N3 C1 C2 -8.0(3) . . . . ?
O1 N3 C1 C2 172.83(17) . . . . ?
O2 N3 C1 C7 172.41(18) . . . . ?
O1 N3 C1 C7 -6.8(3) . . . . ?
C9 C10 C11 C14 69.6(3) . . . . ?
C9 C10 C11 C12 -51.0(3) . . . . ?
C9 C10 C11 C15 -169.7(2) . . . . ?
C7 C1 C2 C3 -0.3(3) . . . . ?
N3 C1 C2 C3 -179.90(18) . . . . ?
C1 C2 C3 C5 -0.4(3) . . . . ?
C1 C2 C3 C4 179.7(2) . . . . ?
C6 C5 C3 C2 0.4(3) . . . . ?
C6 C5 C3 C4 -179.6(2) . . . . ?
N2 C8 C9 O4 6.8(3) . . . . ?
C13 C8 C9 O4 -174.37(18) . . . . ?
N2 C8 C9 C10 -174.78(18) . . . . ?
C13 C8 C9 C10 4.1(3) . . . . ?
C11 C10 C9 O4 -159.9(2) . . . . ?
C11 C10 C9 C8 21.7(3) . . . . ?
N2 C8 C13 O3 0.5(3) . . . . ?
C9 C8 C13 O3 -178.3(2) . . . . ?
N2 C8 C13 C12 -178.48(19) . . . . ?
C9 C8 C13 C12 2.7(3) . . . . ?
O3 C13 C12 C11 146.1(2) . . . . ?
C8 C13 C12 C11 -34.9(3) . . . . ?
C10 C11 C12 C13 57.5(3) . . . . ?
C14 C11 C12 C13 -63.6(3) . . . . ?
C15 C11 C12 C13 176.1(2) . . . . ?
C3 C5 C6 C7 0.2(3) . . . . ?
N1 C7 C6 C5 -179.61(18) . . . . ?
C1 C7 C6 C5 -0.8(3) . . . . ?

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1008199'
